Never mind the nice Jewish girls like Natalie Portman, the most compelling character in today’s pop culture is Amy Winehouse, a Jewish mother’s worst nightmare but still daddy’s little girl
Amy Winehouse in West London, March 17, 2009.
Shaun Curry/AFP/Getty Images
In many ways, this has been the season of the Good Jewish Girl. Next week, the proudly Jewish, defiantly curly-haired Rep. Debbie Wasserman Schultz—a woman “so, so excited  to be Jewish”—will become the second woman to lead the Democratic National Committee. Two months ago, the elegant, shiny-haired, opportunely pregnant Natalie Portman ascended the podium at the Academy Awards to collect the Best Actress Oscar—a day before valiantly standing up  to her sartorial patron in defense of her people. And Portman took this turn as our modern-day Esther shortly after 21-year-old Loren Galler Rabinowitz became the first Jew to compete  for the Miss America title since Bess Myerson won in 1945. “A lot of my friends were taking a gap year in order to make money for school—taking jobs at banks and things,” Galler Rabinowitz said. “I wanted to spend a year doing public service, which I’ve always been extremely passionate about. And this year seemed like my last opportunity before jumping on the hamster wheel of med school.”
All of this earnest Jewish female goodness has been steadily contributing to a feeling in me, one I couldn’t put my finger on until recently.
Even before the Oscars, I stumbled across the celebrity-news report that a British survey  had named Portman as the most desirable celebrity wife. The least desirable? Another Jewess, though bigger-haired and less refined: Amy Winehouse. Winehouse has otherwise fallen out of the news lately. According to most reports, she’s given up hard drugs. Without her daily trips to the store to buy cigarettes in dirty ballet slippers and spontaneous slap fests with concertgoers, Winehouse is now covered merely for wandering  off stage during a concert in Dubai and forgetting the words to her own songs. Back in her Back to Black days, that would’ve been buried at the bottom of a Perez Hilton post, but when alcohol is her only remaining poison, this is perhaps as much as we can hope for. And yet, it is still more than we could get from Portman and that other paragon of femininity with Jewish lineage, Gwyneth Paltrow. Winehouse might throw a glass but never a dinner party.
I miss Amy Winehouse.
Just as Athena sprang fully formed from the head of Zeus, Winehouse came to us from the beehives of the Ronettes, the paradigmatic 1960s girls’ group, with a hairdo that dwarfs theirs by at least a foot. The original bad girls of rock and roll, the Ronettes wore tight, dark skirts and heavy eyeliner—as Winehouse does. But she is by no means a carbon copy of the Phil Spector-produced group, which is best-known for the exuberant single “Be My Baby .” Though she cloaked herself in the style and sound of girl groups from 40 years ago, Winehouse brought a thoroughly modern—and Jewish—sensibility to her lyrics and performances. She spoke not of love and romance, as her predecessors did, but of addictions, sex, and every Jewish girl’s favorite emotion: guilt. In her famously adenoidal voice, she sings about the men she will cheat on, those she will use up, and the ones she intends to spit out. Her songs and tone drip with regret, but also the inevitability of her bad behavior. Any astute listener knows that she’s not going to change. In fact, we hope she doesn’t.
It’s this unrepentant behavior that signals Winehouse’s place in a very different line of Jewish women—not the “nice” ones who make you chicken soup when you’re sick or assure their sons that they’re the smartest boys in the world and any woman would be lucky to marry them. Winehouse’s ancestors are the biblical vixens: Dina, who slept with Shechem; Deborah , the biblical heroine; or, more recently, Monica Lewinsky, the “portly pepperpot” (as the New York Post dubbed her) who nearly ended Bill Clinton’s presidency. These women possessed sexuality so powerful and intoxicating that it influenced national and political outcomes. Still, on “You Know I’m No Good,” Winehouse is most emphatic about another characteristic: her guilt, her seeming regret for all of the things she’s done wrong. It’s as though she’s pounding her chest in synagogue on Yom Kippur, except instead of using the shofar, she confesses her sins above the horns, beats, and drums of Mark Ronson’s production:
And for the sin of cheating on my boyfriend.
And for the sin of thinking of you when I’m trying to please a new guy.
And for the sin of cheating. Yet again.
But she is less concerned in the song with the obvious victim of her infidelity—her guy—than with the other victim of her infidelity: Amy Winehouse. The chorus begins: “I cheated myself/ Like I knew I would.” By being unfaithful she’s lost a good man (who seems to have taken her back at least once). Furthermore, the song’s title shifts some of the blame onto her lover, who should’ve known better before tangling with her. In the last verse she asks, after her boyfriend discovers “little carpet burns” on her arms, “Who really stuck the knife in first?”
Though Winehouse seems to lack the necessary stability and mentality to be a mother, she wants desperately to be one. When asked what she envisions for the future, she insisted , “I’m gonna be looking after my husband and our seven kids.” She frequently dubs herself a “nice Jewish girl,” particularly when she is questioned about her out-of-control persona, as though by stating her desire to settle down and raise children, she can smooth out her dangerous edges. If we think that somewhere down the line, she’ll calm down, sort herself out, and assume a traditional female role, she seems to be suggesting we can let her sow her wild oats without judgment.
Winehouse wasn’t always the bad girl we see warbling, drunk and off key , during live performances. She was once a freshly scrubbed Jewish teen from Northeast London. Back when she recorded her first album, Frank , at 19, she was curvier and wore her long dark hair in loose waves instead of a mammoth beehive. On that album’s cover she is smiling with a full set of teeth, wearing a pink shirt that could’ve easily been pulled from the racks of Topshop. There’s nary a tattoo in sight. True, she had been kicked out of a prestigious stage school for getting her nose pierced, but that’s hardly scaling the mountain of teenage rebellion.
Winehouse’s musical tastes were informed by her family. Her parents and her paternal grandmother, Cynthia, who once dated the legendary musician Ronnie Scott, raised her on a steady diet of jazz greats and soul singers from Billie Holiday to Ella Fitzgerald to Dinah Washington. She seems genuinely close with her father, Mitch Winehouse—the one man in Amy’s life who has lived up to the ideal man she sings about in “Stronger Than Me.” The elder Winehouse has stood by his daughter throughout ordeals with drugs and alcohol and ably manages her finances and career. He even tried to play the guilt card on her by faking a heart attack in order to force her to confront her drug-abuse problems. “I was at me wits end. I just didn’t know which way to turn. I’d tried everything,” he told  the Daily Mirror. “Once I even started screaming said I was having a heart attack, but it didn’t work. Amy’s not stupid and she wanted to see my medical records proving I was actually ill.” Another Jewish father might boast about how his son got into Harvard; Mitch Winehouse talks about he couldn’t fool his addict daughter into believing he was having real chest pains. (Such nachas.)
Amy Winehouse leaves Westminster Magistrates Court, West London, on March 17, 2009.
Shaun Curry/AFP/Getty Images
But despite the obvious pride and care her father shows her and the affection she returns, Winehouse has not always been lyrically kind to him. On her first album, in “What Is It About Men,” she explains why: “Understand, once he was a family man/ So surely I would never, ever go through it firsthand/ Emulate all the shit my mother hated/ I can’t help but demonstrate my Freudian fate.” Instead, she seems to have been most controlled by—and therefore perhaps most influenced by—her grandmother, who hosted weekly Friday-night dinners at her London home for the family. In fact, it was Cynthia’s death in 2006 that has been blamed, at least in part, for Winehouse’s subsequent downward spiral . Winehouse had been a woman grounded by another woman, not by men.
Perhaps this offers a clue to why she changed course for her second album, moving from the adult contemporary jazz sounds of Frank to the sound of to the ’60s American girl groups. At first listen, it might seem highly incongruous to match Winehouse’s explicit lyrics with the melodies and harmonies of the Ronettes. On the track “Me and Mr. Jones (Fuckery) ,” (a reference to Nasir Jones, better known as the rapper Nas), she sings, “Nowadays you don’t mean dick to me.” In the background, the backup singers’ harmonies swell sweetly—“Dick to me,” they repeat after Winehouse. A few verses later, when she sings about Sammy Davis Jr., the backup is at it again, providing unintentional humor. “Best black Jew” rises up and lingers in the air as Winehouse continues.
The first song Phil Spector produced was “To Know Him Is To Love Him,” a ballad whose title was the epitaph on his father’s tombstone. Phil Spector earned his first No. 1 hit with this song, as part of the Teddy Bears. This would be the only time he performed one of his hits; after this point, he would be known only as a producer. The song, which was written as a son’s tribute to his father, becomes a slavishly romantic tune through lead singer Annette Kleinbard’s sweet, artless soprano. Spector backs her on the guitar and harmonizes with the third Bear, Marshall Lieb. This is exactly the kind of a song you’d expect from a man of Spector’s insecurities and neuroses, the kind of man who had been hounded by a domineering Jewish mother for most of his life. What would he want most of all? A woman absolutely devoted to him, one who would say things like, “Just to see that smile/ Makes my life worthwhile.”
It is safe to say that Winehouse could never be that woman, and in her hands the song , which she frequently performs in concert, sounds subtly but critically different. Instead of Kleinbard’s clear, high-pitched tone, Winehouse brings it down several octaves and adds a raspy tinge to her delivery, backed by a simple acoustic guitar. One gets the sense that as Winehouse sings, “Oh, I’ll be good to him/ I’ll bring joy to him,” she is aspiring to be her better self, the kind of woman who is devoted to her man without making demands (perhaps the Jewish mother who dotes on a husband and son, one that Spector wished he had and the type Winehouse wishes to be). This is not a song she could write on her own. Her father has conceded this point. “She’s never gonna write a song about, ‘You look lovely in the moonlight, my darling, give me a kiss,’ ” he told  the Huffington Post in early 2010. “Every song Amy writes is like … [He sticks an imaginary knife into his substantial tum and circles around as though he is eviscerating his entrails.] In Yiddish, it’s ‘schlapping your kishkas [your insides] out.’ Amy’s a great one for schlapping her kishkas—because every song is, like, heartbreak … sorrow … depression.”
If Spector and Winehouse met in real life (say, perhaps, in prison ), it is unlikely that they would find much physical and sexual attraction. Spector is the type of man that she would never end up with—slight, light, and sickly. (One-time band mate Kleinbard once recounted being on a double date in a car with Spector, whose heavy breathing coming from the back she imagined to be heavy petting—until Spector cried out: “I’ve got to get out of here. I’m having an asthma attack.”) In contrast, Winehouse is the one with overwhelming needs, which makes her incapable of meeting those of others. Her compositions tend to be about men who fail to measure up to her standards or, conversely, how she has wronged them. Winehouse does not put her lovers up on a pedestal and is unable to express the slavish devotion a true Spector song (and Spector himself) demands. Even as she sings him promises, it sounds like she already let him down.
This is precisely the type of man Winehouse sings about on her first album, Frank, which established her as an up and coming British singer (and for which she was nominated for the Mercury Prize, a prestigious award). On “Stronger Than Me ” she explains her frustration with a weak man, the type who constantly needs to be bolstered: “You should be stronger than me/ You’ve been here seven years longer than me/ Don’t you know you’re supposed to be the man/ Not pale in comparison to who you think I am.” Her voice on this track is higher and more nasal than it is on “Back to Black,” sort of like the British answer to Fran Drescher. Imagine the nanny issuing this put down: “Feel like a lady/ And you my lady boy.” Accusing her guy of being so feminine that he could easily be mistaken for a transsexual takes shrewish, Jewish nagging to a whole new level.
And even when Winehouse tries on subservience it still comes off as awfully dominant. “I’m not gonna meet your mother anytime/ I just want to grip your body over mine,” she sings a few verses later. Though she describes vanilla, missionary-style sex, the very fact that she’s the one grabbing, placing her partner where she wants him negates her location. Even when she’s the bottom, she’s also the top.
This masculinity that she looks for in men but almost loathes in herself is manifest in her appearance—the bouffant hairstyle, the breasts (surgically enhanced) propped up to her collarbone, the Cleopatra-style eyeliner, the exceptionally tight vintage dresses. All of it represents an exaggerated form of femininity, which is the hallmark of drag. To dress up as Winehouse, a queen would not have to embellish at all. It would not be possible to make the hair any bigger or take the boobs any higher. Her look is prepackaged drag. If she accuses men of acting like women then she too is masquerading—a woman who dresses like a man who dresses like a woman.
So, if Winehouse is too dominant and aggressive—too manly, even—for Jewish men, even most non-Jewish men, who can handle her?
In real life, she’s gone for skinny white junkies who fob off her fame and wealth, but in songs she has teamed up with a beefier sort: African-American rappers. Jay-Z remixed  Winehouse’s monster hit, “Rebab,” while Ghostface Killah sampled the beats, horns, chorus, and some of the verses on a track  of the same name and seems to be in a constant dialogue with her with his rhymes. As Winehouse sings about being “trouble,” he raps in response, “Fight scenes, I take the good with the bad.” But why is he willing to overlook her shortcomings? Because she lives up to the Jewish sex goddess stereotype: “Cuz you give the best brains I ever had.” Winehouse’s ex-husband, Blake Fielder-Civil, made a similar assertion though not in rhyming verse: “She is even better at sex than she is at singing,” he told  a British tabloid. Winehouse’s sexuality is powerful. Yet even Ghostface seems a bit wobbly by the song’s end. On the outro, the rapper repeats the phrase “Got to forgive the past but I never forget it,” as though the memory of his humiliation at the hands of a superior feminine force will somehow keep the pleasurable but ultimately traumatic cycle of infatuation, narcissistic self-fulfillment, and sexual abandonment from repeating itself yet again.
Dvora Meyers is a freelance writer based in Brooklyn. She dressed up as Amy Winehouse for Purim.